Urea → 2-Hydroxy-5-[1-hydroxy-2-(t-butylamino)ethyl]-benzeneacetonitrile

HRID 973246Notes

Reaction equation

[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C1(NC(C)(C)C)C=CC=CC=1.NC(N)=O.C(NN[CH2:27][C:28]([C:30]1[CH:31]=[CH:32][C:33]([OH:39])=[C:34]([CH2:36][C:37]#[N:38])[CH:35]=1)=[O:29])(C)(C)C>>[OH:39][C:33]1[CH:32]=[CH:31][C:30]([CH:28]([OH:29])[CH2:27][NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:35][C:34]=1[CH2:36][C:37]#[N:38]

Participants

Reactant 4

HCID 1176Urea

HCID 6385Tert-Butylamine

HCID 254260N-(1,1-Dimethylethyl)benzenamine

HCID 213251575-[N-(t-butylamino)glycyl]-2-hydroxyphenylacetonitrile

Product 1

HCID 213251472-Hydroxy-5-[1-hydroxy-2-(t-butylamino)ethyl]-benzeneacetonitrile

Procedure

The procedure of Example 1(c) is repeated with substitution of an equimolar amount of t-butylamine for phenyl-t-butylamine in that example. The resulting aminoketone, 5-[N-(t-butylamino)glycyl]-2-hydroxyphenylacetonitrile is reduced according to the procedure of Example 1(d) to yield 2-hydroxy-5-[1-hydroxy-2-(t-butylamino)ethyl]-benzeneacetonitrile.

Sources & evidence

ORD record: ord-3bcf1acb9d32445cb4b832094f928ab6
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04055658

Reaction notes

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